The Best Sailboat Rentals Near Lakeside

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

Excellent staffing at Sterling Sails. We had a great time. Elizabeth and Cody were wonderful. The vessel waa great. Weather was perfect. Couldn't have had a better time. My only gripe was that, after booking, they send you a text message with information, and one of the bulletpoints is an instruction to tip the captain 20%. While i loved the captain, she is awesome, such an instruction violates GetMyBoat's TOS and feels audacious in this economy. (January 2026). It is written as an instruction, not a request, is not mentioned in the GetMyBoat advertisement, and it chips away at the joyfulness of the experience through imposition of pressure to tip. If the boat ownership is not paying their staff well enough, they need to fix that. But to ask consumers to spend $800, and then tell them "wait, now that you've given us $800, we are letting you know you must give us an additional $160," is insanely out-of-touch and quite frankly offensive. Pay your employees better and don't turn a "tip" into a mandatory posr-booking surcharge.

Sail in Modern Luxury Beneteau Oceanis 37 Yacht

Brian was an amazing host! We had a great time celebrating a birthday and Brian couldn’t have been more accommodating and pleasant. His boat is immaculate and very well kept. He even let us drive the boat and taught us some things about sailing. We would highly recommend Brian!

La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California

Top notch experience. I used this as a gift for my staff, as a way to spoil them and start a healing and wellness day together. The Captain was so kind. The accommodations were great. The ride was the perfect amount of time and fun in the sun. Will definitely do this again.

San Diego Bay Sailing Experience

Aaron was awesome! Very fast communication, friendly, and has fair and upfront pricing with no hidden fees. The boat was amazing too and he even had wine ready to go for us to drink while we sailed. He took some great photos while I proposed to my girlfriend and helped make this an unforgettable experience. 10/10 would recommend him to anyone!

San Diego Bay Sailing Experience

THANK YOU AARON!!! The boat was excellent and the ride was smooth all the way. My friends and I truly enjoyed the experience which, for me, made my birthday weekend!!! I really loved that Aaron was a true fly on the wall while we had a ball on the boat. I recommend San Diego Sailing Experiences to EVERYONE. BOOK AARON!

San Diego Bay Sailing Experience

The entire experience was great! I selected this listing because I have sailed on this type of vessel before and liked it. Aaron was communicative from the start and made everything very easy. Once on board he was easy going and friendly, told us whatever we wanted to know, provided wine and snacks and the cutest puppy to play with if we wanted to! The weather was beautiful, Aaron is a great sailor and guide and we couldn't have loved it more. We arrived a few minutes late and at the end he offered us more time at no charge to compensate for the missed time, which was really nice. We plan to come back during the Jan - March time frame and will definitely hit up Aaron for a trip out to see the Whales! Highly recommend. Don't look further!